Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5350)
Drug Name
Nifurtimox
Synonyms
NIFURTIMOX; Lampit; Bayer 2502; 23256-30-6; BAY 2502; Nifurtimox [INN:BAN]; Nifurtimoxum [INN-Latin]; CCRIS 2201; EINECS 245-531-0; CHEBI:7566; C10H13N3O5S; 4-Thiomorpholinamine, 3-methyl-N-((5-nitro-2-furanyl)methylene)-, 1,1-dioxide; 4-((5-Nitrofurfurylidene)amino)-3-methylthiomorpholine-1,1-dioxide; 3-Methyl-N-[(5-nitro-2-furanyl)methylene]-4-thiomorpholinamine 1,1-dioxide; 3-Methyl-4-(5'-nitrofurylidene-amino)-tetrahydro-4H-1,4-thiazine-1,1-dioxide
Indication Chagas disease [ICD11: 1F53] Approved [1]
Trypanosomiasis [ICD11: ICD11: 1D51-1F53] Phase 4 [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 287.29 Topological Polar Surface Area 117
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
6842999
ChEBI ID
CHEBI:7566
CAS Number
23256-30-6
TTD Drug ID
D0FC1J
Formula
C10H13N3O5S
Canonical SMILES
CC1CS(=O)(=O)CCN1/N=C/C2=CC=C(O2)[N+](=O)[O-]
InChI
InChI=1S/C10H13N3O5S/c1-8-7-19(16,17)5-4-12(8)11-6-9-2-3-10(18-9)13(14)15/h2-3,6,8H,4-5,7H2,1H3/b11-6+
InChIKey
ARFHIAQFJWUCFH-IZZDOVSWSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Nifurtimox M1 DM005117 N. A. Reduction - Reduction 1 [4]
Nifurtimox M10 DM005123 N. A. Reduction - Reduction 1 [4]
Nifurtimox M11 DM005108 N. A. Oxidation - Oxidationn 1 [4]
Nifurtimox M12 DM005109 N. A. Oxidation - Oxidationn 1 [4]
Nifurtimox M13 DM005119 N. A. Reduction - Reduction 1 [4]
Nifurtimox M14 DM005120 N. A. Reduction - Reduction 1 [4]
Nifurtimox M15 DM005111 N. A. Other reaction - Nucleophilic reaction 1 [4]
Nifurtimox M16 DM005110 N. A. Oxidation - Oxidationn 1 [4]
Nifurtimox M17 DM005118 N. A. Reduction - Reduction 1 [4] , [6]
Nifurtimox M18 DM005112 N. A. Other reaction - Nucleophilic reaction 1 [4]
Nifurtimox M2 DM005116 N. A. Reduction - Reduction 1 [4]
Nifurtimox M3 DM005115 N. A. Reduction - Reduction 1 [4]
Nifurtimox M4 DM005106 N. A. Other reaction - Nucleophilic reaction 1 [4]
Nifurtimox M5 DM005107 N. A. Other reaction - Nucleophilic reaction 1 [4]
Nifurtimox M6 DM005113 N. A. Reduction - Reduction 1 [4]
Nifurtimox M7 DM005121 N. A. Reduction - Reduction 1 [4]
Nifurtimox M8 DM005122 N. A. Reduction - Reduction 1 [4]
Nifurtimox M9 DM005114 N. A. Reduction - Reduction 1 [4]
Nitrite DM006704
946
Unclear 1 [3]
Nifurtimox M5 DM005107 N. A. Unclear 2 [4]
⏷ Show the Full List of 20  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005539 Nifurtimox Nifurtimox M4 Other reaction - Nucleophilic reaction Unclear [4]
MR005541 Nifurtimox Nifurtimox M11 Oxidation - Oxidationn Unclear [4]
MR005542 Nifurtimox Nifurtimox M12 Oxidation - Oxidationn Unclear [4]
MR005543 Nifurtimox Nifurtimox M16 Oxidation - Oxidationn Unclear [4]
MR005544 Nifurtimox Nifurtimox M15 Other reaction - Nucleophilic reaction Unclear [4]
MR005545 Nifurtimox Nifurtimox M18 Other reaction - Nucleophilic reaction Unclear [4]
MR005546 Nifurtimox Nifurtimox M5 Other reaction - Nucleophilic reaction Unclear [4]
MR005547 Nifurtimox Nifurtimox M6 Reduction - Reduction Unclear [4]
MR005548 Nifurtimox Nifurtimox M9 Reduction - Reduction Unclear [4]
MR005549 Nifurtimox Nifurtimox M3 Reduction - Reduction Unclear [4]
MR005550 Nifurtimox Nifurtimox M2 Reduction - Reduction nfsB [4]
MR005551 Nifurtimox Nifurtimox M1 Reduction - Reduction nfsB [4]
MR005552 Nifurtimox Nifurtimox M17 Reduction - Reduction nfsB [4], [6]
MR005553 Nifurtimox Nifurtimox M13 Reduction - Reduction Unclear [4]
MR005554 Nifurtimox Nifurtimox M14 Reduction - Reduction Unclear [4]
MR005555 Nifurtimox Nifurtimox M7 Reduction - Reduction Unclear [4]
MR005556 Nifurtimox Nifurtimox M8 Reduction - Reduction Unclear [4]
MR005557 Nifurtimox Nifurtimox M10 Reduction - Reduction Unclear [4]
MR005558 Nifurtimox Nitrite Unclear POR [3]
MR005540 Nifurtimox M4 Nifurtimox M5 Unclear Unclear [4]
⏷ Show the Full List of 20 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
NADPH-cytochrome P450 reductase (CPR) DME0076 Homo sapiens
NCPR_HUMAN
1.6.2.4
[3]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DME1048 Escherichia coli
NFSB_ECOLI
1.5.1.34
[4]
Xanthine dehydrogenase/oxidase (XDH) DME0070 Homo sapiens
XDH_HUMAN
1.17.1.4
[5]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
2 ClinicalTrials.gov (NCT00906880) Clinical Study to Assess the Tolerability, Feasibility and Effectiveness of Nifurtimox and Eflornithine (NECT) for the Treatment of Trypanosoma Brucei Gambiense HumanAfrican Trypanosomiasis (HAT) in the Meningo-encephalitic Phase. U.S. National Institutes of Health.
3 Absorption, Metabolism, and Excretion, In Vitro Pharmacology, and Clinical Pharmacokinetics of Ozanimod, a Novel Sphingosine 1-Phosphate Receptor Modulator
4 Structural and Mechanistic Investigation of the Unusual Metabolism of Nifurtimox
5 Metabolization of nifurtimox and benznidazole in cellular fractions of rat mammary tissue
6 Nifurtimox activation by trypanosomal type I nitroreductases generates cytotoxic nitrile metabolites

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